Potassium Carbonate → HCID 25211814, compound

HRID 1409833Notes

Reaction equation

HRID 1409833 reaction equation
Cl[CH2:2][C:3]([NH:5][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C:14]2[S:15][C:16]([C:19]3[C:23]([CH3:24])=[C:22]([C:25]([F:28])([F:27])[F:26])[O:21][N:20]=3)=[CH:17][CH:18]=2)=[O:13])[CH2:7]1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>C(#N)C>[CH3:35][N:36]1[CH2:41][CH2:40][N:39]([CH2:2][C:3]([NH:5][C@H:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([C:14]3[S:15][C:16]([C:19]4[C:23]([CH3:24])=[C:22]([C:25]([F:28])([F:27])[F:26])[O:21][N:20]=4)=[CH:17][CH:18]=3)=[O:13])[CH2:7]2)=[O:4])[CH2:38][CH2:37]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 68565012HCID 68565012, compound

Product 1

HCID 25211814HCID 25211814, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloro-N—{(S)-1-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carbonyl]-piperidin-3-yl}-acetamide (35 mg, 0.08 mmol, as prepared in Example 56) was dissolved in acetonitrile (3 mL) containing anhydrous K2CO3, treated with N-methylpiperazine (18 μL, 0.16 mmol), and stirred for 3 days. The reaction mixture was then evaporated and treated with water to provide a homogeneous solution which was extracted with EtOAc (2×4 mL), dried over MgSO4, filtered, and evaporated to afford product as an foam (34 mg, 85%). 1H NMR (CDCl3) 1.60-1.76 (m, 3 H), 1.88-1.98 (m, 1 H), 2.22 (s, 3 H), 2.29 (d, J=1.3, 3 H), 2.32-2.52 (m, 8 H), 2.92 (s, 2 H), 3.52 (br s, 1 H), 3.48 (br s, 2 H), 3.72-4.46 (m, 3 H), 7.32-7.44 (br m, 3 H). 19F NMR −63.1. LC/MS 4.59 min, [M+1]+ 500.

Workup

  1. customThe reaction mixture was then evaporated
  2. additiontreated with water
  3. customto provide a homogeneous solution which
  4. extractionwas extracted with EtOAc (2×4 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-25addf401ae3484ebf6fce19744ba9bd
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

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